EP 0463162 A1 19920102 - PREPARATION OF 5,6,7-TRINOR-4,8-INTER-m-PHENYLENE PGI 2 DERIVATIVES.
Title (en)
PREPARATION OF 5,6,7-TRINOR-4,8-INTER-m-PHENYLENE PGI 2 DERIVATIVES.
Title (de)
VERFAHREN ZUR HERSTELLUNG VON 5,6,7, -TRINOR- 4,8,-INTER-m-PHENYLEN PGI,2 Abkömmlingen.
Title (fr)
PREPARATION DE DERIVES DE 5,6,7-TRINOR-4,8-INTER-m-PHENYLENE PGI 2.
Publication
Application
Priority
- JP 4687389 A 19890227
- JP 4687489 A 19890227
- JP 9000237 W 19900227
Abstract (en)
-prostaglandin-I2 derivs. of formula (I) are synthesised from dibromo dihydro-cyclopenta(b)benzofuran (II): (where R3 and R4 are H or methyl; R2 is methyl or ethyl) by (1) Prins reaction to give 1-(hydroxymethyl) -2-hydroxytetrahydro, -5,7-dibromo-cyclopenta(b)benzofuran; (2) Grignard reaction with alkyl 3-formyl propionate followed by removal of the 7-bromo atom by catalytic hydrogenation to give cpds. (III): (3) protection of the 2-hydroxyl with an alkanoyl group and oxidation to the 1-aldehyde; reaction with (MeO)2P(O)CH2COCHR4CH2C=CR2; (5) reduction of the carbonyl group and deprotection.
Abstract (fr)
La présente invention se rapporte à un procédé de synthèse de dérivés de 5,6,7-trinor-4,8-inter-m-phénylène PGI2 [VII] à partir de 3a,8a-cis-dihydro-3H-5,7-dibromocyclopenta[b]benzofurane (1). La présente invention se rapporte également à deux intermédiaires (8) et (11) utilisés pour la préparation du composé (1).
IPC 1-7
IPC 8 full level
A61K 31/557 (2006.01); A61P 7/02 (2006.01); C07C 41/16 (2006.01); C07C 43/247 (2006.01); C07D 307/93 (2006.01)
IPC 8 main group level
C07D (2006.01)
CPC (source: EP US)
A61P 7/02 (2017.12 - EP); C07C 43/247 (2013.01 - EP US); C07D 307/93 (2013.01 - EP US); C07C 2601/10 (2017.04 - EP US)
Designated contracting state (EPC)
AT BE CH DE DK ES FR GB IT LI LU NL SE
DOCDB simple family (publication)
EP 0463162 A1 19920102; EP 0463162 A4 19920520; EP 0463162 B1 19940511; AT E105555 T1 19940515; AU 5107790 A 19900926; AU 634213 B2 19930218; CA 2028626 A1 19900828; CA 2028626 C 19971209; DE 69008851 D1 19940616; DE 69008851 T2 19940818; DK 0463162 T3 19940620; ES 2053180 T3 19940716; FI 106715 B 20010330; FI 905315 A0 19901026; JP 2527277 B2 19960821; JP 2836556 B2 19981214; JP H08225561 A 19960903; NO 176962 B 19950320; NO 176962 C 19950628; NO 904668 D0 19901026; NO 904668 L 19901227; US 5202447 A 19930413; US 5420310 A 19950530; WO 9010003 A1 19900907
DOCDB simple family (application)
EP 90903426 A 19900227; AT 90903426 T 19900227; AU 5107790 A 19900227; CA 2028626 A 19900227; DE 69008851 T 19900227; DK 90903426 T 19900227; ES 90903426 T 19900227; FI 905315 A 19901026; JP 33113095 A 19951127; JP 50365290 A 19900227; JP 9000237 W 19900227; NO 904668 A 19901026; US 60178391 A 19910102; US 95735792 A 19921120